


Hell's secretary

by Coll_is_kinda_gay



Category: Supernatural
Genre: Bondage, M/M, Past Abuse, Past Rape/Non-con, Past Torture, Spoilers, Torture, Wing Kink
Language: English
Status: In-Progress
Published: 2020-05-31
Updated: 2020-06-03
Packaged: 2021-03-03 02:08:06
Rating: Explicit
Warnings: Major Character Death, Rape/Non-Con
Chapters: 4
Words: 4,591
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24417142
Author URL: https://archiveofourown.org/users/Coll_is_kinda_gay/pseuds/Coll_is_kinda_gay
Summary: You had been Lucifer's secretary and personal sex object for many years. After that, you were Crowley's. You were devoted to hell and would do anything for it or it's ruler. You would even give your life if it was needed.You had been kidnapped by the Winchesters inevitably. They wanted you for information. You were very valuable to both of their biggest threats. Lucifer and Crowley. You had information, power, and the hearts of both the demon uking and the ex-king. They may have been ruthless, abusing you and torturing you, but they did love you behind it all.When everything seemed perfect, that was when you were inevitably captured by the Winchesters. Your personality was what won over the hearts of both Cas and Dean. They finally understood why you had kept your position all these years. When you became a demon that was when your mental filter dropped. You were charismatic and charming, yet you only truly cared for whoever was on hell's throne.
Relationships: Castiel (Supernatural)/You, Castiel/Dean Winchester, Crowley (Supernatural)/You, Dean Winchester/You
Comments: 3
Kudos: 25





	1. Prologue

**Summary for the Chapter:**

> Basically an extended version of the summary.

You sat at Crowley's feet, a leash attached to the collar around your neck that read, "(Y/N)". You were only allowed to speak when given permission, so you sat in silence, staring up at him. Your legs were going numb from sitting still for so long.

A low rank demon burst into the throne room, clearing his throat and pausing for a moment to regain his composure before hurriedly walking up to Crowley. He bowed to both of you before speaking, "My king, I know you didn't want to be bothered-"

"Then why are you here? Why aren't you torturing souls or making contracts?" Crowley glared at him. He had plans to spend some "quality time" with you.

You shiver at the thought. If Crowley wasn't satisfied with your performance, he would punish you for sure.

"I'm sorry, but it's the Winchesters. They want a deal with you."

"I'm listening..."

He grimaced, "In person..." the demon rocked on his feet, "I would highly suggest not going yourself, my king. It could be a trap."

Crowley nodded, turning to you, smiling to see you had stayed still, "(Y/N), you've been good lately. Be a dear and go see what they want. You deserve to stretch your legs anyway."

You nod, hugging his leg in thanks.

He chuckles, unclipping the leash from your collar before ruffling your hair, "Now, go! ...Before I change my mind!"

You smile, getting up on your wobbly legs and hurrying off.

As your legs were still numb, your senses were tampered. The demon moved his foot into your path, tripping you. You faceplanted, grunting in pain as your previous cuts and bruises hit the stone cold ground along with your nose, which was now broken and bleeding.

You stood up, cupping your nose to stop the blood from staining your shirt.

"No one hurts him but me!" Crowley roared. A flap of demonic wings could be heard as he disappeared from his throne and reappeared in front of the inferior demon, "I suggest you apologize before I tear your limbs from your body."

"S-Sorry..." he mutters, not daring to meet his eye.

Crowley huffs, "Pet, you have permission to speak and move freely if you have any input."

You growl at the demon in front of you, grabbing his chin in your hand. Your blood smeared onto his face, "S-S-Sorry!~" you say mockingly, "You wanna give that another try?"

Crowley crosses his arms, smirking.

"Sorry... (Y/N)..." the demon didn't look you in the eye.

"Again!" you yell into his ear.

"I'm sorry Mr. (Y/N)!" he yells back.

"Tell me what you're sorry about!" you yell louder.

"I'm sorry for tripping you!"

"And?~"

"A-And for breaking your nose..." he finally looks at you, guilt and regret in his eyes.

"I guess I'll let your sorry ass live..." you release his chin, "But the next time you mess up, there will be no hesitation!" you pat his cheek twice, leaving a bloody handprint, "May I leave now?" You ask Crowley.

Crowley nods, hiding his enjoyment underneath his gaze.

As the doors close behind you, you hear screaming from the demon, begging Crowley to let him go. The king was not that merciful.

............

You stood in front of Cas and Dean, glaring at them, "I'm here, now what do you want?" They had you on a devil's trap.

Cas stepped forward, "You're wearing a... Collar?"

Dean shakes his head, "We wanted Crowley, not some succubus... or whatever the male equivalent is..."

"I promise you, squirrel, I am better than him. And, for your information, it's incubus."

"I've heard that name before... (Y/N)..." Castiel mutters, repeating your name over and over.

"How the hell are you better than the king himself?!" Dean yells.

"I'm practically his second in command," you say proudly, puffing your chest a bit.

Castiel's eyes widen, realising where he knew you from. He leaned over to Dean, whispering something.

Dean nods in understanding, "You should have never left his side, little man..." he looks to Cas, "Cuff him."

You grin, "Kinky, are we?" you lift your wrists, presenting them to Cas with an eyebrow wiggle.

"Unlike my brother, I would never bang a demon. Especially a dude."

"You weren't saying things like that the other night..." Cas says gruffly. He locked the handcuffs around your wrists.

"Shut up, Cas!" Dean yells.

"As you wish..."

"You know these cuffs can't hold me, right?" you ask, rolling your eyes as Dean broke the devil's trap.

"Mhm, yeah... You tell yourself that," Dean got out his phone calling someone.

While Dean is busy, Cas pats you down and removes the items from your pockets. You had a knife and a small red box that was sort-of a tracker. Cas recognises it and smashes it under his foot.

"Yeah, uh. We got a situation, look up anything about a demon named (Y/N)... Uh huh... Yeah... Ok we'll bring him in." Dean hung up, "Alright, let's do this shit," he went to the Impala, grabbing a burlap sack, some duct tape, and a set of soundproof headphones.

"No way you're putting those on me," you try to fly away, but the handcuffs stop you.

Dean chuckles, "The fuck we aren't." He rips a piece of duct tape free with his teeth and places it over your lips.

You try and bite his hand, failing.

Cas grips you hard, pulling your body flush with his chest.

Dean pulls the burlap sack over your head and then you feel the headphones fall over your ears. Shortly after, a rope is tying your arms to your body and another is tying your legs together. One of them picks you up and throws you in the trunk.


	2. Chapter 1

**Summary for the Chapter:**

> First day in the bunker's dungeon.

**Notes for the Chapter:**

> I spent a lot of time thinking of what I wanted to do with this chapter, but I think I'm satisfied with what I made

You awoke shirtless and chained to the wall. Your arms had locks just below your elbow, stopping much movement.

Castiel was standing a few feet in front of you, looking you over, "These wounds are from Crowley himself?" he gestured to the many cuts and bruises along your chest, stomach, and arms.

You nod, not able to speak as the duct tape was still over your mouth.

Castiel reaches forward and grips the tape off in one swift motion.

You wince, some of your vessel's skin coming off with it.

"Why? You're already practically his slave. Why hurt the person who knows him the most?" Cas tilts his head at you.

You didn't know how to respond. Thankfully, you didn't have to as Dean came running into the dungeon, "It's Sam! They got Sammy!"

You feel a grin forming on your lips.

"Why you little- You had something to do with this didn't you?!" Dean threw himself at you with his Purgatory blade in his hand.

Cas stops him with just one arm, "He's far too valuable, Dean. You can't kill him."

Dean sighs, not calming down, but backing off.

You smirk, leaning forward towards them, "Crowley will make you pay for this~"

"Why does he care that we have you? He's the damn king, he can get himself another secretary," Dean's gaze was filled with fire.

"I'm not just any old secretary, my boy. I've been the secretary to the king since before Lucifer was in the cage."

"So, Crowley has a... soft... spot?" Cas questions.

"He's probably torturing the moose as we speak, trying to get information on what happened to me."

"Oh, I'll kill you asshole, do not test me," Dean growls.

"Mhm, Do it. See what Crowley does to your precious brother~"

Dean spins on his heel, leaving the room.

Cas looks from the door to you and then back a few times.

"You're cute when you're confused~" you grin at him.

"I'm not confused, just... indecisive."

"You had a friend... Another demon, I believe she went by Meg? She called you Clarence... May I ask why?"

"I'm not talking about this..." he pulled up a chair in front of you, "I am merely staying here to babysit."

"I just find it intriguing that a demon and an angel were fond of each other. How does that even happen?"

"She was nice to me. She didn't give me a reason to despise her and, I do believe everyone deserves a second chance," he takes off his trench coat, hanging it across the back of the chair before taking a seat.

"Mhm... Even me? Even Crowley?"

"If you were willing... Yes."

You scoff slightly, "Honey, there is nothing in here worth saving," your eyes turn black, "Pure demon is left in this vessel..."

"There is nothing 'pure' about it."

"Now you get the picture, Clarence!"

"Do not call me that!" his eyes were practically glowing with rage.

You grin, shaking your head lightly, "Aww, did I strike a nerve... Clarence?"

He stands, invading your personal space. His hand came down on your throat, holding your head against the wall, "Normally I'd be against torture, but maybe I'll make an exception... Just for you..."

"Do it, I'd love to be the demon who made Castiel, the angel who fell in love with humanity, break."

He growls, letting go of you angrily before going to the cabinet of devices, surveying them before deciding on his angel blade.

You feel yourself laugh, pulling on your restraints, "Do. Your. Worst."

.......

Dean's POV:

I heard screams coming from the dungeon, but I didn't care. I was way too angry with that cocksucker. Crowley had Sammy and I had to get him back.

I grabbed a beer from the fridge and tried to remember the spell I needed to summon him. I didn't use it before because I figured it wasn't needed, but clearly I was wrong. Sam was always better at remembering things... He completed me, and I don't know if I could ever live without him.

.......

2 hours later...

I cut open my hand and squeezed it into the bowl, chanting the Latin phrase that was required before waiting for the king to arrive.

"Hello, squirrel..." Crowley stood on the devil's trap I had painted onto the floor, "I think you have something that belongs to me?"

"Yeah, and you have something of mine... But I've gotta keep your toy for a little longer. I think Cas is trying to get information from him as we speak," I say, wrapping my hand in a cloth to stop the bleeding.

"Then why am I here?" Crowley crosses his arms, "I assumed we could make a deal? A sort of hostage trade? Your brother for my boy?"

"No. At least... Not yet."

"Yet?" He looked angry but there was also a hint of jealousy and nervousness in his eyes and in the way his shoulders were tensed.

"Yes... Yet. You see, I was going to make a different deal with you, but you gave us something even better."

He uncrosses his arms, "I did, didn't I? Well, guess it's what I get for being lazy."

There was a muffled scream coming from the dungeon.

"(Y/N)..." his mask fell for a moment, showing his worry.

I scoff, "So that's why he's so sure you'll save him. The demon king actually has feelings... Who would'a thunk..."

"Shut up..." he tries to throw me to the wall but nothing happens. He sighs softly, "Are we done here? Can I go?"

"Nah, I thought it'd be good to have both the king and his pet. That way I can keep the advantage."

"You can't be serious..."

"Even if I did let you go, how do I know you're not gonna go try and bring (Y/N) with you?" he gestures with his hand.

"Good point..."

"So, instead I think I'll wait for Cas to finish and then we'll put you in the dungeon too."

"Bollocks."

......

30 mins later...

Castiel's POV:

I walk out of the dungeon, leaving behind a heavily bloodied demon behind me. My hands were stained red along with my white shirt, splattered with his blood. I sigh, going to the main room of the bunker.

"Dean I-" that's when I saw Crowley, "Why is he here?"

"I figured two hostages is better than one... It honestly can't hurt," Dean shrugs, "Can you take care of him, get him in the dungeon?"

"...Fine," I use my grace to clean myself up, approaching the demon in front of me.

"I shouldn't have come..." Crowley mutters.

I shake my head, making a pair of demon handcuffs appear in my hand.

"You think that'll work on me?" he asks, scoffing slightly.

"Y'know, that's the same thing your boy said to us," Dean says, taking a swing of his beer.

I nod, taking Crowley's moment of realization to put the cuffs on him.

Dean gets up, scratching the devil's trap with his knife.

Crowley headbutts me, surprising me only slightly as I tighten my grip. I feel my nose bleed, dripping off my lips.

Dean grabs him by one arm and I take the other, guiding them down to the dungeon.

(Y/N) perks up when he hears footsteps, but his face pales when he sees Crowley in cuffs.

"Nothing to worry about, pet. We'll figure a way out of this," he says, giving him a fake smile. But (Y/N) knew him well enough to see the uncertainty behind it.

I grab one of the demon-proof collars, putting it around his neck, "That should keep him secure..." The collar was connected to a chain, long enough for him to stand but that was about it.

Dean steps forward, shoving Crowley into a wooden chair next to the wall opposite (Y/N), securing his arms to the arms of the chair.

......

(Y/N)'s POV:

After Dean left to sleep, leaving Castiel with you and Crowley you spoke up, "How come he gets a chair? My feet hurt... I want a chair..." you pout.

Castiel scoffs, "Behave, and I might just switch you to one."

"I am your king after all... I deserve only the best... Anyways, you shouldn't even be speaking right now, I have not given you permission," Crowley says.

"What are you gonna do? Punish me?~ Last I checked we've been kidnapped. You can't even touch me right now~"

"I hate you..." he snarls.

"Yeah yeah, I love you too."

"Well, I'll leave you two to 'stew in your juices' as Dean would say," Cas leaves the room.


	3. Chapter 2

**Summary for the Chapter:**

> Playtime with the boys

A few days pass. Crowley was feeling the beginning of withdrawal from human blood. He was angry, weakened, but still hopeful. You knew what he looked like in withdrawal, he lashed out more, he would sweat a lot, to the point where you didn't like sleeping in the same room as him, and worst of all, he used you more, for torturing and other things you tried not to think of right now. You did love the man, but you didn't want to pop a boner right now, especially with Castiel watching you intently.

Castiel spent a lot of time just sitting next to you, sometimes he would stand in front of you, leaning close to whisper observations into your ear. You could tell by the daggers Crowley glared at him that he hated it. He didn't want anyone to be as close to you as Castiel got unless it was himself.

Dean didn't come around much, but one day both of them came into the dungeon, giving each other sideways glances and chuckling to themselves.

"Bloody hell are you two so happy about?" Crowley snarls.

"You care about your boy very much, don't you?" Dean asks.

"We thought, maybe we could get you to tell us where you're keeping Sam. And we," Cas gestures between him and Dean, "Can get our own pleasure out of it too..."

That was when you realized, your face covered in shock, "You don't mean-"

"Don't you tucking touch him! I'll kill you!" Crowley yells, "I-I'll kill- I'll kill you..." his voice got softer and he trailed off.

"Mhm, you do that... But first I need my brother back," Dean leans against the wall, a small smirk on his lips.

Castiel approached you, trailing a hand down your chest. He heals the marks from what he did earlier, "Is it okay if I do this?" he whispers into your ear.

You mutter back a yes, "I've been eyeing you ever since I first saw you."

Cas messes with your belt, kissing and licking at your neck.

You bite your lip, uncomfortable with Crowley and Dean in the room.

Crowley had closed his eyes, not wanting to watch. Meanwhile, Dean was watching Castiel's every move.

Cas bends down and removes your shoes, massaging your feet lightly before coming back up to the button on your pants. He wanted to take his sweet time with you.

You let out an involuntary groan, your feet sore from standing for so long.

Cas eases your pants off, pulling your boxers with them. You were left completely nude and on display for all three men in the room.

You whimper, looking at Crowley to see if he's opened his eyes yet.

Cas gets on his knees, lifting your legs over his shoulders. His face was mere inches away from your half-hard cock.

You sigh, glad your feet and legs finally get a break from the constant pressure.

Cas starts licking and kissing at your dick, not taking it in his mouth or sucking just yet.

Dean walks over to you, "Am I allowed to play too?~" he whispers into your ear.

You feel yourself nod, too busy looking down at the angel between your thighs to even think about speaking.

Crowley opens his eyes, taking a peek. He immediately regrets it, growling slightly. His eyes turn black, with jealousy, hatred, and lust. He couldn't help but imagine himself doing that to you. He wasn't ready to give up just yet, holding out on telling them where Sam is.

Your cock fully hardens as Cas takes you in his mouth, making eye contact with you while slowly bobbing his head.

Dean gently rests a hand on the back of Cas' head, muttering praise. He kisses you just as gentle. He tasted of whiskey and beer, not actually all that unpleasant versus Crowley's kisses. They always tasted like blood and sulfur.

You moan into Dean's mouth, pulling against your restraints. You wanted to bury your hands in Cas' hair so bad.

Crowley stays silent, looking at the floor. He tried to ignore how much you were enjoying this, digging his fingernails into his palms.

Cas speeds up his pace, dragging his tongue along the underside of your cock.

Dean leans back slightly, moving his kisses to your neck. His hands came down and grab your ass, pulling your cheeks apart and kneading.

You moan, unable to keep your sounds in.

Crowley shifts uncomfortably in his seat, the chain on his neck rattling.

Dean steps back, petting Cas' hair lightly before going to Crowley, "I bet you're secretly enjoying this, you sick perv."

You pull on your restraints, opening your eyes to look at Crowley. He never treated you with this much care, it was always about him.

Cas pops off of your dick, the resulting sound something you'd only ever heard in porn. "I bet you're just begging me to let your arms free, aren't you?" he chuckles, letting your legs fall off his shoulders.

You whine, too scared to say it out loud.

"Alright, tell you what..." he stands, loosening his tie and unbuttoning his shirt a bit, "I can't let you out of that iron, so I'll just give you a show. Is that good?"

You nod, your dick twitching slightly at the idea.

Cas smiles, easing his shirt off his shoulders.

Dean began to hum careless whisper, joking around. He was kneeling next to Crowley, "See? My boy's much better than yours, knows what his lover wants and he always gives."

Cas slowly removes his belt, looking at you with a smirk on his face.

"And now, for the main event!" Dean cheers, clapping. He leans closer to Crowley muttering something into his ear.

"Oh, please..." Crowley whimpers, "Yes, I am enjoying this. You happy now? You get what you want?"

Dean mutters something else, gently trailing his hand down to Crowley's groin. He unzips his suit pants, reaching in and releasing his member from it's clothed prison.

Cas unzips his own pants, letting them drop to the floor as he steps out of them. He was wearing white lace panties and knee high socks with garters.

Dean whistles, "Love it when he plays dress up!"

Your eyes trail down Cas' body, stopping at the bulge straining against the thin material between his dick and the air. "Your wings... Can I see them?" you build up the courage to ask. You always loved how beautiful an angel's wings are. Almost made you wish you were born angel and not demon. Almost.

Cas looks taken aback, "Usually I save them for just Dean and I... I-I don't... I don't know..."

Dean stands from his place on the floor, hugging Cas from behind. "It's okay love, he can see them..."

Cas nods, "Alright..." his wings slowly emerge from his back, pushing Dean away with their raw strength. He flexes them a bit when they become fully visible.

Crowley gasps in awe, but also fear in how powerful an angel's wings are.

You smile, "Beautiful..."

Dean nods in approval, "I think we can let the Prince down from the wall... something tells me to trust him."

Cas looks over his shoulder at Dean before nodding. He grabs the key from his slacks, which were still on the floor, and unlocks your restraints.

You rub your arms where the iron had touched your skin, nodding in thanks.

Cas pulls you into a kiss, rubbing his clothed erection against your bare one.

You moan softly, your fingers grabbing onto Cas' wing and tugging on some of the feathers.

Crowley growls lightly, angry that you could have your way but he couldn't.

You give him an apologetic look over Cas' shoulder, a silent promise to make it up to him.

To be continued...


	4. Chapter 3

"(Y/N)... Why aren't you running for help? Please, leave this place! Do it for your king!" Crowley began speaking softly but quickly became yelling at you.

You jump up into Castiel's arms, "I'll do as I damn well please, you have no power over me from where you sit," you wrap your legs around Cas' waist, holding on tight, one hand in his wing and the other on his shoulder.

Cas chuckles into your ear, "Oh, I like you~" he presses your back against the wall, licking and sucking at your neck.

Dean echoes with his own laugh.

You throw your head back, giving Cas better access.

Crowley growls, "All of you will pay for this..."

Dean unzips his own pants, pulling out his cock from it's denim prison. He begins stroking himself, enjoying the show.

Cas continues grinding against you, "Ready to give up yet, Crowley? I have your little boy toy practically in the palm of my hand."

"Never..." he spits in Cas' direction, but it lands several feet short of hitting him.

You whine, "Cas, quit with the talk and just fuck me... I can show you, I am much more than just a 'toy'," you mutter, just loud enough for him to hear.

Cas nods, setting you down on your feet before taking off his boxers. He flips you around, pushing you forward so you would bend over in front of him.

You tense up, fully prepared for him to just shove himself in. You were surprised when a lubed finger teases your puckered hole.

Cas frowns, "Relax..." he gently kneads at your cheeks.

You nod, resting your arms against the wall for support.

Cas finally pushes a slender finger into you, followed by a second when he realizes you were already prepared for it. He starts fucking you with his fingers, hitting your sweet spot on every other stroke.

You spread your legs more, letting out surprised moans every time he hits it.

Cas slowly starts scissoring his fingers, taking his free hand to rub your hip gently.

"Ah... Please Cas..." You moan.

He leans in close to your ear, "Please what?"

"Please, fuck me... I'm ready," you shiver, pressing your ass against him.

Cas snaps and suddenly his boxers are off, "As you wish, handsome~" he pulls a chair over and tugs you down onto his lap.

You bite your lip in anticipation, grinding your ass against him.

Cas lifts your hips, lining himself up with your entrance. He then thrusts into you, bottoming out in one swift movement.

You cry out, moaning Cas' name.

Dean walks over, pulling his shirts off. He grins as he sees your eyes trail along his body.

Crowley closes his eyes, not wanting to watch anymore. A silent tear rolls down his cheek.

Cas starts moving your hips up and down, gently thrusting in and out of you.

Dean gets on his knees in front of you, "Mind if I...?" he gestures to your cock, bobbing in the air.

You shake your head quickly, "No, I-I don't-... I don't mind..." You moan as Cas brushes against your prostate.

Dean takes your cock in his hand, wrapping his lips around the tip.

Cas grins over your shoulder, "Dean's really good at that... Just relax and let us take care of you..."

You nod, moaning softly.

Dean starts bobbing his head, stroking from your head to your base and then repeating. Each pass of his lips, he buries his nose into your skin and nuzzles you softly.

You watch him, your breathing picking up.

Cas continues thrusting into you, kissing along your neck and shoulder.

Dean picks up his pace, gagging slightly at a particularly harsh thrust from Cas.

You moan, "Fuck, I-I'm close!"

"Go ahead and cum whenever you're ready, (Y/N)... You don't have to hold it in for Dean, he can take it," Cas mumbles into your ear.

You nod, shaking slightly as your release barrels through you, making your toes curl.

Dean drinks up every drop he can, some spilling out of the corners of his mouth. He pops off of your cock, grinning widely.

Cas speeds up, chasing his own release. He fucks into you hard and fast, making you whimper with overstimulation.

Dean licks his lips and wipes his chin with the back of his hand.

Suddenly Cas bottoms out, releasing deep inside you.

You whine softly, closing your eyes.

Dean shushes you, standing up to capture your lips in a gentle kiss.

Cas pulls out, mumbling praise into your ear as he came down from his high.

You sigh softly, kissing Dean back. You could feel Cas' cum leaking from your ass.

Dean smiles into the kiss and leans back, "You alright? You need water? A snack?"

"I appreciate the concern, but demons don't eat."

He nods, "Alright... I guess I'll leave you and Cas to clean up."

Cas gently lifts you from his lap, healing any damage he had caused your rear.

....

A few hours pass since Cas and Dean had left you in the dungeon. Cas had cleaned you up and dressed you before strapping you to a chair identical to the one Crowley was in.

Crowley looks up at you, "Why did you let them do that...?" he had tears in his eyes, "I love you, (Y/N)... Don't you get that?"

You look down at your feet, mumbling an apology.


End file.
